en don't really get middle-aged, real-life-style, touchy-feely movies
made about them in the way women do. Cinematic portrayals of male
friendship tend to be of the Swingers school—male bonding through
scoring babes, rather than the more feminine motif of bonding by
suffering through one's girlfriends' too-human shortcomings. Director
and screenwriter Alexander Payne (Election, About Schmidt) manages to
combine both the male and female traditions in Sideways, a middle-aged
male buddy bonding movie about human weakness, forgiveness, and scoring
babes.

A subtly written and executed treatment of Rex Pickett's "Sideways: A
Novel", Sideways, the film, attempts to unravel itself slowly and
gently, spending more time on character development than most films—almost too much, in fact, clocking in at 123 minutes of slow, steady
unfulfillingness.

The premise is engaging enough: sensitive, nebbish protagonist and wine
snob Miles (Paul Giamatti) and has-been actor and all-around LA dude
Jack (Thomas Haden Church) set off for a week in southern California
wine country a week before Jack's wedding. What Miles hopes will be a
week of bourgeois testosteronity—golf, wine-tasting—is in Jack's
mind a perfect opportunity to get laid as much as possible before his
wedding.

The next step is a ribald game of Truth or Dare...

Though the film is seen through the vaguely more sympathetic lens of
Miles, it's hard to tell which of the two friends is, really, more
fucked up. Whereas Jack is quintessentially shallow, deceitful to
himself and others, fairly amoral and obsessed with poontang, Miles has
sublimated a lifetime of self-prophesied disappointments into unhealthy
obsessions with wine and his own failure. As the friends encounter a
pair of enthusiastic, eligible California wine-loving ladies, each
becomes more disappointed with the other as the week wears on. Jack,
unable to exercise self-control or respect for his friendship with
Miles, is frustrated and pushy with his gun-shy friend’s inability to
“close the deal” with waitress Maya (played here blandly by Virginia
Madsen). Miles, on the other hand, finds it harder and harder to stand
by philandering Jack, who seems to have everything Miles wants (while
Jack is at least a has-been, Miles is simply a never-was) and is yet
willing to squander it all for a chick who pours wine (Sandra Oh).

While the film strains for depth, dwelling on a pithy allegory of the
fragility and fleetingness of special wine with the precarious charms
of life (we are at one point subjected to a vaguely insipid soliloquy
in which Miles describes himself under the thin guise of Pinot Noir),
it often fails to reach it meaningfully. Though Giamatti and Church’s
portrayals are gentle and finely wrought, the nature of their
friendship is questionable. Are they really learning lessons about life
and love, vulnerability and risk, as the film might seem to suggest? Or
is Miles really just a huge doormat hanging out with a caring, but
ultimately opportunistic, jerk?

"Dude, that was the most careless plastic surgeon I've ever seen..."

Dew-eyed Giamatti is compelling here as Miles, but it’s a little hard
to feel compassionate towards the character after Jack walks all over
him for the nth time. Some of it’s in the name of comedy, sure—but
this is buddyism beyond the call of duty, and eventually it reflects
more poorly on Miles than Jack. The film’s unfinishedness—which is to
say, it’s unclear raison d’etre rather than its intentionally
open-ended conclusion—is really its crippling flaw. It seems
reasonable that Jack would care for Miles, especially since his
esteemless friend serves willingly as a glorified lackey, but why would
supposedly intellectual, sensitive Miles continue to abide Jack? For
all its evenly paced detail, the film seems to leave this essential bit
of irrational soul out: it never provides a convincing argument for why
these two losers still love and tolerate each other so deeply, other
than perhaps that they are both just that shallow and desperate, which
isn’t really a satisfying answer at all.

That said, Sideways is in many senses better grounded in the real world
than many of its contemporaries. For a film that seeks to both
entertain and be realistic, it does both adequately well, weaving a
couple of truly poignant moments (almost entirely courtesy Giamatti’s
rich expressiveness) through its languid tapestry. Perhaps only
middle-aged men will find this actually hits home, but at least it hits
near.